Most Helpful Guy

Play 21 questions. I guarantee you that if you do you will have no problem keeping a conversation going.

Don’t ask her to play 21 questions! That’s not what I mean when I say “play 21 questions”. Simply ask questions. If you ask a question, you’re going to get an answer, and that answer will lead the conversation in any variation of directions.

When you hit a dead end, ask another question! You would be surprised how easy it actually is to keep a conversation going using this method.

Not only is it easy, it marks you as someone who has interesting things to say and likes to communicate. If you ask funny questions on occasion which make her laugh you'll have three major bonus points heading your way!